“Dolly, you are a very unique woman,” his email began. Nice beginning. I was thrilled to hear from Charles again. Funny to hear him call me unique, since he was one of my most unique Dolly Date regulars. I say that about Charles because he and I had enjoyed many a Dolly Date together, but we had never had sex. Nor, for that matter, oral sex, mutual masturbation, kissed–except in a socially warm, on the cheek sort of a kiss. I know that I am paid for my time and companionship, but sheesh, didn’t he want MORE?! Still, how could I complain, I went to great locations, dined in fabulous restaurants, enjoyed amazing spas while he attended to business meetings or conventions or whatever. So “no fuck Chuck”, my private nickname for him, a nickname which I never spoke aloud, was calling me “unique”. He had my attention.
“You are the kind of person who seems to have a mysterious source of positive energy. You are always making the people around you laugh and smile. You are always a wonderful person to be around. And of course you are gorgeous. You have the body of an athlete, a sexy athlete to be sure, since you were a professional tennis player; you are tall, fit, toned and slim. I am beguiled by your blonde hair that reaches your mid-back, by how well you take care of yourself. You are always well put together and looking very fashionable. Your skin is always smooth with a perfect tan and she have those dazzling, shiny, white teeth in your perfect smile. The list of your attractive features goes on and on, from your deep blue eyes that pull me in, to your toned legs and trim, flat toned waist, your amazing ass, and your eye-grabbing bust. You are just perfect.”
“Flattery will get you everywhere with me, Charles, not that you need to flatter me,” I was thinking as I read his letter. A woman rarely reacts badly to being called “perfect” or reading a man’s laundry list of things about her that turn him on. And then I thought to myself again, “but he’s still never even TRIED to fuck me! He mentions my ass, my tits, says I’m just perfect. What do I have to do to get laid with this man?! He certainly tips me enough!”
Okay, I like to win, and successfully seducing a man, even a paid Dolly Date is still a seduction, and I hadn’t given Charles the pleasure I know I can bring a man. True confession–He had become an obsession. Fucking Chuck. I don’t know how many hours I’ve spent fantasizing about touching him intimately, feeling and squeezing his manhood, licking it, having him take my body.
Over the last few years, I’ve let him know I love spending time with him, how fine of a gentleman he is, that I’d never let anything between us impact his outside life, and how I think about him and imagine us spending our time together even more intimately. That his desires could be satisfied just for the asking. Sigh, he still had never asked. Yet our small talk, our familiarity with each other, likes, dislikes, tastes in food, wine, films, even a preference for one overnight express company over another. He knew my cycle, for goodness sake. Hey, now that I think about it, I could have increased my revenue days by scheduling Dolly dates with him during “cycle” days when I ordinarily would not have had dates, since he wasn’t into the sex. But that’s not me, that’s not Dolly I’m at my best for every date, always ready for whatever may come. Or in Charles’ case, ready for had never cum.
Still, every time we became closer, I celebrated a small victory. Of course, I still had delusions that I would actually get to make love to him. “Dolly,” he would say, in my pre “unique email” dates, “don’t worry about that, I love being with you, love waking up to you, falling asleep with your scent filling my senses and my bed, your wit, laugh, how you make me feel just by being my companion.” Sure there are tougher ways to earn the generous gifts I took home from these trips. My ego took a hit as I started to resign my poor neglected pussy to the realization that it would probably not happen. All the same, I didn’t give up.
And then I got the email that told me I was unique and an invite to his retreat home near Palm Springs, California. Such a fun airport. The concourse for the larger planes is named after Sonny Bono. And then you pass Kirk Douglas Way and Gene Autry Trail. I used to visit that area when I was on the tennis circuit, and the Indian Wells Tennis Garden still hosts a great tournament every March, one of the few non-Grand Slams that bring the men and the women together. Ah, such fantastic sex memories from those tournaments, my “friends” on the mens tour seemingly as glad to see me as I was to see them. And with sexy women all around, well, many people checked off some bucket-list items involving threesomes and more-somes in that beautiful desert setting. Which perhaps adds to my frustrated feelings of un-fulfillment with Charles, after all, he lives in an area that I associate with mind-altering life-long memory instilled sex, and this fine gentleman hadn’t even let me suck his cock yet!
I can’t name the exact town where Charles’ place is, of course, not just for his privacy but also for the public figures whose own getaway homes were in the same enclave or those nearby. I’d been to his lovely place out there before, it was built on a golf course so it was typically a place he went without his wife, who preferred a lake home that was just an hour’s drive from their main residence in the city where his company was headquartered. Ironically, the yacht from my family’s shipbuilding business was most often enjoyed by Charles’ wife at the lake house.
Charles’ driver and car were waiting for me at the airport, and after a drive though the beautiful Coachella valley, we arrived and his house manager greeted me again warmly (He was called a house manager because “butler” just would not be the right word for everything Donald did throughout the grounds and the home as well as the out-buildings).
I got unpacked, settled in to the room where ostensibly we could claim I was staying merely as a houseguest, which did afford me the use of my own luxurious en-suite, though everyone knew we shared a bed. I wondered, though of course couldn’t ask, if anyone else except Charles and I knew that we shared the bed but did not share lovemaking or any other sexual intimacies. I accepted the glass of my favorite wine that Donald offered me when I stepped out to just sit in the shade of the outdoor section of the house and look at the mountains and admire their beauty and not long after, Charles arrived. I turned to greet him when I heard his voice, and when I did he looked like he was stunned. Why, I wondered, he’d seen me like this before. Hell, he’d seen me naked as I would strip to sleep, or neglect a robe in the bedrooms, always having hoped he’d give in to my temptation, though he never had. I was wearing a very sexy looking workout outfit, a tight tank-top on with a purple skirt that just covered my fit, toned, fuck-friendly ass. My tanned, toned, sexy fitness-fanatic legs were exposed right up to my upper thighs and I wore strappy, high heeled sandals which showed off my recently-painted, skirt-matching purple toenails. Why was this look stunning suddenly? He couldn’t take his eyes off of my legs as I approached him, embraced him with a close, sensual hug and a tender soft kiss to his cheek, before I took his hand to guide him beside me as I returned to the amazingly comfortable soft and sat down. I smirked at him with a wink, one of my trademark moves with him.
“My god, you look great Dolly!” he managed. “I never get over how beautiful you are!”
Didn’t I already tell you that flattery would get him everywhere with me. EVERYWHERE.
I laughed and thanked him and then asked him about his trip, his day and week. He spoke but didn’t pay attention. He just stared at the various parts my appearance that captivated him. My hands that playfully touched his arm or clasped fingers with his hand, my manicured fingernails raking his skin from time to time, my sculpted toned arms and perfectly tanned skin, my full, shiny lips, long golden hair, and he seemed to be looking deeper into my blue eyes than ever before. Was I crazy or was something that I’d wanted for so long finally happening between us?
Donald’s calm, familiar remote voice told us through an intercom that refreshments were on the table behind us. Hadn’t even noticed anyone had been so close. How long had we been sitting there together? No clock, no wristwatch, no cell phone nearby. Time stood still at the getaway house. Donald knew when people had to be somewhere, or when to get ready to do so. We turned, looked at the fruit, vegetables, light antipasti, charcuterie, and more of our wines along with sparkling and still waters, and stood to go make a couple plates. Suddenly Charles stopped and kissed me on the cheek and hugged closely, passionately even though not sexually. But even without hands on my ass or tits or his tongue in my mouth, I knew this was different. He didn’t usually hug me in a way that allowed me to feel his stiffening cock press into me. What did that mean? For some reason this time he didn’t pull away like he usually did. I loved this new boldness and hoped there was more to follow. Much more.
We broke the hug and made plates, refilled our wine, and sat at edges of the table together, closely, intimately watching each other snack and make more innocuous small talk. As ever, his wife was never discussed. He did ask about my father, the yacht-building business, and how my children and parenthood was going. I’d met Charles initially at an exclusive high end boat and yacht show where he was a buyer, and I’d charmed him and introduced him to Daddy and he’d purchased a yacht from us. We’d stayed in touch, and I was taken by surprise when he offered to hire me to accompany him to a business conference in Vail during ski season. Um, he didn’t seem to know about the Dolly Date aspect of my life, yet here he was offering to hire me?
“Your time is valuable, Dolly, and the quality of my life and ability to enjoy the parts of my life that are away from my family is of value to me. I’d be taking you away from other business opportunities, you will incur costs to make other arrangements for your children, it seems only right. And not to speak of the fact that if I didn’t have such a lovely friend as you, my other choices would be either loneliness or hiring a professional escort as my lovely companion. Her time would be compensated, so why shouldn’t yours?”
Okay, um, how the hell to answer that? It was all perfectly true, it made more sense than he could have imagined, considering that if I said “no” he’d likely search for someone else and possibly find … ME! “Besides, Dolly, any escort I’d hire –and don’t look so shocked, it happens, it’s not like you hear about on TV or in movies, I’ve got friends, and they’ve told me these are professional upscale ladies, please don’t judge me, but anyway, I’m pretty sure if I ever did do that I’d just be looking for someone who looked like you, anyway. You are the lady I enjoy these friendly times with.”
So he’d thought about hiring escorts, but ironically wanted me instead? Was this all a ruse? Had he stumbled across my website, years after meeting me and start to compare those shots without my face or head to how I appeared when clothes professionally while in his presence? Or was this a wholly innocent but monumentally coincidental offer by a man who was none the wiser?
I’m not dumb. “Charles, your lovely company, a trip to Vail, and a consulting fee, we’ll call it, as well? Only a fool would say ‘no’. I accept.”
And that was how we’d started. He knew me so much better than most of my Dolly date friends. Though those of you reading this who know all those things about me too know that Charles was not completely unique, though he was definitely among an elite group. As we finished our lovely food, I felt the warmth of the wine, the warmth of the later afternoon radiant heat, and the hope that Charles might at long last enjoy all that I had to offer.
We went back to the outdoor sectional, so comfortable, and we just talked and laughed together. I began to contemplate how I would get my chance to make a move.
So I slipped off my sandals, resigning myself that while it is always sexy as hell to fuck a man while still wearing heels and digging those heels into his ass while he drove his manhood home into my fitness model turned MILF body, and pulled my feet up onto the couch between us. I extended them a little farther towards him. Charles started to rest his hand on my leg and slowly run his fingers across my skin. I extended my feet right out onto his lap. I rested my hand across his leg, close to where I saw a thickness getting more pronounced. He touched my leg far more deliberately slowly started to rub it. How far would he go?
“Dolly, I have to confess something. I really love that outfit you have on. In fact, I’ve been thinking about how great you look in it all this time… I think purple might be your color.”
He continued sliding his hand up and down my calves. His erection was growing as Charles inspected my glowing skin. Again, I felt his cock press into my legs. I wanted him to know I felt it.
I starting to move my feet back and forth across his lap against his shaft. He closed his eyes. I’ve given foot jobs, before, and I knew I gave a good one. Charles was not getting any satisfaction at home. I could tell what he was feeling was amazing. I felt whatever private, inner line he’d drawn for us being erased, wiped away.
“I meant only you. There’s no one else. I know you know I’m married, you’ve told me you understand. And I don’t want to lead you on, I’m not leaving her. I love that we can be together. She probably thinks I’ve been sleeping around for years anyway and seems to accept how things are. Um, unique, yes, I guess that means to me, you are the only one so special for us to share this kind of relationship. Oh I know you have other boyfriends Dolly, whatever you want to call the other men in your life, and I know you’re no longer married but since I haven’t made love to you I’m sure someone must have been….”
I nodded yes. He saw, seemed relieved, and continued.
“Ah, yes, whatever, yes… so, I love that we can share what we’ve always shared, and now that I’ve finally realized how special you are, what I called “unique”, well, I’m so happy that I’ve finally sampled what I was missing by not sleeping with you before.”
I didn’t think the time was right to point out that vacationing with me, taking me as his companion, sharing his bed with me even if not consummating the physical act of sex sort of was “sleeping” around. In fact, it was more sleeping than happened with most men I have “slept with”. The next morning as the sun rose over the valley and the mountains cast their shadows, and as we enjoyed the coffee for Charles and herbal tea for me that Donald had left on a tray outside Charles’ door fifteen minutes before sunrise, Charles chuckled as he shared the same realization about sleeping together and the meaning of that phrase. But he’d flattered me, declared me special. I hoped I was special enough for repeat performances, I darn sure loved my first sexual liaison with him.
THE END
Purely fictional fantasy for your reading enjoyment!